Synthesis and reactions of 3-halomethyl-substituted oxazine N-oxides

Mikhaylov, Andrey А.; Dilman, Alexander D.; Kunetsky, Roman A.; Khomutova, Yulia A.; Стручкова, Марина И.; Korlyukov, Alexander A.; Ioffe, Sema L.; Tartakovsky, Vladimir A.

doi:10.1016/j.tetlet.2009.12.066

Cited by 8 publications

(4 citation statements)

References 24 publications

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“…The low yield of 1a and conversion of enamine 3a in the reaction with NiBr 2 may be associated with its poor solubility in organic solvents (Table 1, entry 11). In the case of CuBr 2 , the major product was found to be 3‐bromomethyl‐substituted cyclic nitronate 6a , probably arising from an electrophilic bromination of bis(oxy)enamine 3a (Table 1, entry 14) 11d. The best result was obtained with anhydrous cobalt(II) bromide in THF (Table 1, entry 15).…”

Section: Resultsmentioning

confidence: 99%

A General Metal‐Assisted Synthesis of α‐Halo Oxime Ethers from Nitronates and Nitro Compounds

Sukhorukov

Kapatsyna

Yi³

et al. 2014

Eur J Org Chem

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An approach to the synthesis of α‐halo oxime ethers from readily accessible nitronates and nitro compounds via bis(oxy)enamines is reported. A key step of the strategy involves the unprecedented reaction of bis(oxy)enamines with a metal (Co, Zn, Mg, Mn) halide that acts as both a promoter and halide (Br, I, Cl) source. A variety of cyclic and acyclic ethers of α‐halo oximes, including previously unavailable trimethylsilyl ethers of α‐iodo oximes, have been synthesized in good‐to‐high yields.

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Section: Resultsmentioning

confidence: 99%

A General Metal‐Assisted Synthesis of α‐Halo Oxime Ethers from Nitronates and Nitro Compounds

Sukhorukov

Kapatsyna

Yi³

et al. 2014

Eur J Org Chem

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“…The electrophilic activity of the nitronate 2h, containing a halomethyl group at C-3, might appear in two different fashions nucleophile addition at the C]N bond, or its halogenation. 18 Fortunately, the nitronate 2h (R 0 ¼ Br) reacted with the silyl Scheme 1 Retrosynthesis via Mannich-disconnection of scaffold 1.…”

Section: Resultsmentioning

confidence: 99%

“…The electrophilic activity of the nitronate 2h, containing a halomethyl group at C-3, might appear in two different fashions nucleophile addition at the C]N bond, or its halogenation. 18 Fortunately, the nitronate 2h (R 0 ¼ Br) reacted with the silyl Table 1 Silyl ketene acetal addition to five-membered cyclic nitronates 2 a ketene acetal in a usual fashion, to give the respective nitroso acetal 3h (trans/cis ¼ 8 : 1).…”

Section: Resultsmentioning

confidence: 99%

Three-step assembly of 4-aminotetrahydropyran-2-ones from isoxazoline-2-oxides

Naumova¹,

Mikhaylov²,

Khomutova³

et al. 2014

RSC Adv.

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Tetrahydropyran-2-ones with a 4-amino function connected to a tertiary carbon atoma widely naturally occurring fragmentare constructed by a three step protocol from easily available isoxazoline 2-oxides. In the first stage, the carbon skeleton of the target product is formed upon a C,C-coupling of a silyl ketene acetal with a nitronate function, under silyl triflate catalysis. The key step of the assembly consists of the oxidative cleavage of an endocyclic NO bond of intermediate cyclic nitroso acetals with mCPBA, accompanied with lactone ring closure, and gives rise to b-nitro-d-lactones in 63-85% yields. The latter are reduced with amalgamated aluminium, to furnish the target scaffold.

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“…In contrast to the corresponding reaction of N , N ‐bis(siloxy)enamines 13 , halogenation of N ‐alkoxy‐ N ‐siloxyenamines 15 derived from cyclic nitronates 14 affords α‐halo‐substituted nitronates 71 , which are usually not converted into nitroalkenes (Scheme ) . Halogenation can be performed with I 2 , Br 2 or NBS.…”

Section: Nitrones and Nitronates As α‐C‐nucleophilic Synthonsmentioning

confidence: 99%